Nitric Acid → HCID 178470076, compound

HRID 37488Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:30])[NH:8][C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:19][CH:18]=2)=[CH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].[N+:31]([O-])([OH:33])=[O:32].O>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:30])=[N:8][C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:19][CH:18]=2)=[C:10]([N+:31]([O-:33])=[O:32])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2]

Participants

Conditions

Temperature: -20 °C

Procedure

In 3 ml of acetic anhydride was dissolved 1.0 g of 3,4-diethoxycarbonyl-6-(4-methoxyethoxymethoxyphenyl)-2-pyridone, and the mixture was cooled to -20° C. and thereafter 0.2 ml of fuming nitric acid was added dropwise. After the mixture was stirred for 1 hour, water was added. After 2 hours' stirring at room temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride, and dried. After the solvent was distilled off the resulting crystals were collected by filtration with diethyl ether.

Workup

stirringAfter 2 hours' stirring at room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with an aqueous solution of sodium hydrogencarbonate, water
dry with materiala saturated aqueous solution of sodium chloride, and dried
distillationAfter the solvent was distilled off the resulting crystals
filtrationwere collected by filtration with diethyl ether

Sources & evidence

ORD record: ord-3d53c54a2e4f4cab99301c738e54a2b5
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420275

Reaction notes

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